European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 8

Early View (Online Version of Record published before inclusion in an issue)

Editor: Haymo Ross, Deputy Editor: Susan Wilkinson

Impact Factor: 3.154

ISI Journal Citation Reports © Ranking: 2013: 14/58 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry

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  1. 1 - 79
  1. Full Papers

    1. Design of Organocatalysts

      Remote Substituent Effects on the Stereoselectivity and Organocatalytic Activity of Densely Substituted Unnatural Proline Esters in Aldol Reactions

      María de Gracia Retamosa, Abel de Cózar, Mirian Sánchez, José I. Miranda, José M. Sansano, Luis M. Castelló, Carmen Nájera, Ana I. Jiménez, Francisco J. Sayago, Carlos Cativiela and Fernando P. Cossío

      Article first published online: 3 MAR 2015 | DOI: 10.1002/ejoc.201500160

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      Densely substituted enantiopure proline esters obtained through [3+2] cycloadditions catalyze aldol reactions. These synthetic organocatalysts produce different enantiomeric aldol adducts depending on the stereochemical dispositions of the substituents at distal positions with respect to the catalytic site. Design criteria are proposed for this kind of organocatalysts.

  2. Short Communications

    1. Glycosylation

      Phenyliodine Bis(trifluoroacetate) (PIFA) as an Excellent Promoter of 2-Deoxy-2-phthalimido-1-thioglycosides in the Presence of Triflic Acid in Glycosylation Reactions

      Tetsuya Kajimoto, Koji Morimoto, Ryosuke Ogawa, Toshifumi Dohi and Yasuyuki Kita

      Article first published online: 2 MAR 2015 | DOI: 10.1002/ejoc.201500186

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      Glycosylation reactions using p-(octyloxy)phenyl 2-deoxy-2-phthalimido-1-thio-D-glucopyranoside or p-(octyloxy)phenyl 2-deoxy-2-phthalimido-1-thio-D-galactopyranoside as the donor substrate afforded β-glycosylated products in good to excellent yields by activating the thioglycosides with PIFA (1 equiv.) and TfOH (2 equiv.).

  3. Full Papers

    1. Ligand Synthesis

      A Facile Route to Bis(pyridyl-1,3,5-triazine) Ligands with Fluorescing Properties

      Matthias F. Geist, Daniel Chartrand, Mihaela Cibian, Fabian Zieschang, Garry S. Hanan and Dirk G. Kurth

      Article first published online: 2 MAR 2015 | DOI: 10.1002/ejoc.201403521

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      Several bis(pyridyl-1,3,5-triazine) (dpt) ligands are prepared via Stille coupling with yields and scope of application superior to known trimerisation procedures. Ditopic ligands with different spacers are prepared and incorporation of p- and m-substituted phenyl rings enable access to different isomers. The absorption and emission properties can be tuned using oligothiophene spacers.

    2. Drug Synthesis

      A Stereoselective Catalytic Nitroaldol Reaction as the Key Step in a Strategy for the Synthesis of the Renin Inhibitor Aliskiren

      Sergio Rossi, Maurizio Benaglia, Riccardo Porta, Livius Cotarca, Paolo Maragni and Massimo Verzini

      Article first published online: 2 MAR 2015 | DOI: 10.1002/ejoc.201403659

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      A new strategy for a convergent synthesis of the first-in-class orally active direct renin inhibitor aliskiren has been developed.

    3. Fluorinated Compounds

      Synthesis of Trifluoromethyl-Containing Polysubstituted Aromatic Compounds by Diels–Alder Reaction of Ethyl 3-Benz­amido-2-oxo-6-(trifluoromethyl)-2H-pyran-5-carboxylate

      Ivan S. Kondratov, Nataliya A. Tolmachova, Violetta G. Dolovanyuk, Igor I. Gerus, Constantin-Gabriel Daniliuc and Günter Haufe

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201500032

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      Reactions of ethyl 3-benzamido-2-oxo-6-(trifluoromethyl)-2H-pyran-5-carboxylate with cyclic alkenes and terminal acetylenes are useful for the efficient and selective preparation of trifluoromethyl-containing polyfunctionalised aromatic amino acid derivatives.

    4. Glycoside Synthesis

      A Practical Synthesis of Various 2-Deoxy-N-glycosides by Using D-Glucal

      Terence J. Meyerhoefer, Sonia Kershaw, Nadia Caliendo, Sumeia Eltayeb, Emi Hanawa-Romero, Polina Bykovskaya, Victor Huang, Cecilia H. Marzabadi and Michael De Castro

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201500001

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      A series of 2-deoxy-2-iodo-N-glycosides were prepared by using D-glucal, N-iodosuccinimide, trimethylsilylacetamide, urea, imidazole, pyrrolidinone, and benzotriazole in good to excellent yields. Removal of iodine from C-2 of the newly generated 2-deoxy-2-iodo-N-glycosides led to formation of various 2-deoxy-N-glycosides.

    5. Substrate-Specific Cyclisation

      Preparation of Pyranose-Based Thioimidate N-Oxides (TINOs)

      Stéphanie Marquès, Marie Schuler and Arnaud Tatibouët

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201403619

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      Previously unknown pyranose-based thioimidate N-oxides (TINOs) were prepared by two strategies based on the cyclisation of suitably functionalised thiohydroximate functions anchored on various carbohydrate backbones, either through a Mitsunobu-type reaction or through desilylative cyclisation.

  4. Short Communications

    1. Hydrosilylation

      Stable and Easily Handled FeIII Catalysts for Hydrosilylation of Ketones and Aldehydes

      Kailong Zhu, Michael P. Shaver and Stephen P. Thomas

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201500090

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      The iron(III)-catalysed hydrosilylation is reported for the operationally simple reduction of ketones and aldehydes (20 examples, 55–93 % yield).

  5. Full Papers

    1. Racemization

      Racemization of Olefinic Alcohols by a Carbonyl(cyclopentadienyl)ruthenium Complex: Inhibition by the Carbon–Carbon Double Bond

      Madeleine C. Warner and Jan-E. Bäckvall

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201500066

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      Racemization of various sec-alcohol substrates containing a carbon–carbon double bond catalyzed by Ru(CO)25-C5Ph5)Cl was investigated. A strong inhibition of the rate of racemization was found for substrates having a C3–C5 chain with a terminal double bond. Alcohol substrates with a di- or trisubstituted double bond were found to give less inhibition of the racemization rate. The racemization reactions were studied by NMR spectroscopy with the aim of detecting intermediates.

    2. Dihydroxylations Revisited

      Asymmetric Dihydroxylation of Esters and Amides of Methacrylic, Tiglic, and Angelic Acid: No Exception to the Sharpless Mnemonic!

      Fabian Weber and Reinhard Brückner

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201403622

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      The Sharpless mnemonic is generally accepted as a predictive tool for the stereochemical outcome of Sharpless asymmetric dihydroxylation reactions. However, it was claimed that isobutyl tiglate is dihydroxylated with the opposite facial selectivity because of a preference for a “Chapleur transition state”. We have investigated this claim and proved it false.

    3. Annulated Heterocycles

      Carbonylative Synthesis of Phthalimides and Benzoxazinones by Using Phenyl Formate as a Carbon Monoxide Source

      Sujit P. Chavan and Bhalchandra M. Bhanage

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201500109

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      A simple and efficient palladium-catalyzed carbonylative cyclization of N-substituted 2-iodobenzamides and 2-iodoanilides was investigated for the synthesis of phthalimides and benzoxazinones, respectively, by using phenyl formate as a CO source.

    4. Cross-Coupling

      Nucleophile-Selective Cross-Coupling Reactions with Vinyl and Alkynyl Bromides on a Dinucleophilic Aromatic Substrate

      Lu-Ying He, Mathias Schulz-Senft, Birk Thiedemann, Julian Linshoeft, Paul J. Gates and Anne Staubitz

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201500138

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      A nucleophile-selective one-pot cross-coupling reaction on an aromatic compound bearing both a stannyl group and a boronic ester has been developed with vinyl and alkynyl bromides as electrophiles, exploiting the different reactivity of the Stille and Suzuki–Miyaura cross-coupling reactions. The typical roles of the aromatic ring as the dielectrophile coupling to vinyl and alkynyl metal species are reversed, which presents a new tool for organic synthesis.

  6. Short Communications

    1. Asymmetric Fluorination

      Organocatalytic Asymmetric Fluorination of 4-Substituted Isoxazolinones

      Huanrui Zhang, Baomin Wang, Longchen Cui, Xiaoze Bao, Jingping Qu and Yuming Song

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201500046

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      A straightforward method for the asymmetric fluorination of 4-substituted isoxazolinones catalyzed by a bis-cinchona alkaloid catalyst was developed. A series of 4-fluoroisoxazolinone derivatives with a fluorine-containing quaternary stereocenter were obtained in good to high yields with good enantioselectivities (up to 91 % yield, 85 % ee).

  7. Full Papers

    1. Arene Hydrogenation

      Facile Arene Hydrogenation under Flow Conditions Catalyzed by Rhodium or Ruthenium on Carbon

      Tomohiro Hattori, Takashi Ida, Aya Tsubone, Yoshinari Sawama, Yasunari Monguchi and Hironao Sajiki

      Article first published online: 25 FEB 2015 | DOI: 10.1002/ejoc.201500050

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      A variety of aromatic compounds in iPrOH solution are readily hydrogenated to the corresponding saturated carbocyclic or heterocyclic compounds during a single pass of approximately 20 s through a catalyst cartridge packed with 10 % Rh/C or 10 % Ru/C together with hydrogen gas under relatively mild conditions.

    2. C–H Activation

      Palladium-Catalyzed C–H Bond Acylation of Acetanilides with Benzylic Alcohols under Aqueous Conditions

      Feihua Luo, Jun Yang, Zhengkai Li, Haifeng Xiang and Xiangge Zhou

      Article first published online: 25 FEB 2015 | DOI: 10.1002/ejoc.201500016

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      Palladium-catalyzed dehydrogenative coupling reactions between acetanilides and benzylic alcohols under aqueous conditions are reported. A wide range of benzophenone derivatives could be obtained in good to excellent yields up to 98 %. Mechanism studies showed that a bimetallic palladium cyclopalladated complex might be involved in the catalysis.

    3. Bioactive Neolignans

      A Diastereoselective Route to trans-2-Aryl-2,3-dihydrobenzofurans through Sequential Cross-Metathesis/Isomerization/Allylboration Reactions: Synthesis of Bioactive Neolignans

      Rémy Hemelaere, François Carreaux and Bertrand Carboni

      Article first published online: 25 FEB 2015 | DOI: 10.1002/ejoc.201500019

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      The development of a highly diastereoselective synthesis of trans-2,3-dihydrobenzofurans based on a cross-metathesis/isomerization/allylboration sequence is reported. This new approach was efficiently employed for the preparation of natural neolignans.

  8. Short Communications

    1. Reaction Mechanisms

      On the Mechanism of Phenolic Formylation Mediated by TiCl4 Complexes: Existence of Diradical Intermediates Induced by Valence Tautomerism

      Carlos Heras, Iván Ramos-Tomillero, Marc Caballero, Marta Paradís-Bas, Ernesto Nicolás, Fernando Albericio, Ibério de P. R. Moreira and Josep Maria Bofill

      Article first published online: 25 FEB 2015 | DOI: 10.1002/ejoc.201403548

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      The mechanism of phenolic formylation mediated by TiCl4 has been investigated both theoretically and experimentally. Stable diradical intermediates induced by valence tautomerism have been detected and characterized. These diradical species are expected to be of fundamental significance in organic and bioorganic chemistry.

    2. Hydro-Heteroarylation

      Remote Amide-Controlled Gold-Catalyzed Stereoselective Hydro-heteroarylation of Acrylamides: Access to Pyrido[3,4-b]indoles

      Himanshu H. Butani, Dipak D. Vachhani, Umed C. Bhoya, Anamik K. Shah and Erik V. Van der Eycken

      Article first published online: 25 FEB 2015 | DOI: 10.1002/ejoc.201403682

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      The amide functionality is used as a remote control for the stereoselective hydro-heteroarylation of acrylamides. This gold-catalyzed carbocyclization provides a diversity-oriented and concise route to biologically important pyrido[3,4-b]indoles. Moreover, the adverse effect of silver salts on this hydro-heteroarylation is also studied; U-4CR = Ugi 4-component reaction.

    3. Nitrogen Heterocycles

      A General Synthesis of Bis(o-azaheteroaryl)methane Derivatives from N-Oxides of Azines and Azoles

      Magdalena Szpunar and Rafał Loska

      Article first published online: 23 FEB 2015 | DOI: 10.1002/ejoc.201500072

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      1,3-Dipolar cycloaddition between N-oxides of azines or azoles and in situ generated terminal difluoroalkenes provides a general method of the synthesis of bis(o-azaheteroaryl)methane derivatives containing different 5- and 6-membered heterocyclic units. Selected products were used for the preparation of two new unsymmetrical analogues of BODIPY fluorescent dyes.

    4. Vinyl Iodides

      Copper(I)-Catalyzed (Z)-β-(Tosyloxy)alkenyl Iodide Synthesis from (Aryl)[(E)-β-(tosyloxy)alkenyl]iodonium Tosylates: Diversity-Oriented Synthesis of Trisubstituted Alkenes

      Keshab Mondal and Subhas Chandra Pan

      Article first published online: 23 FEB 2015 | DOI: 10.1002/ejoc.201500039

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      A highly efficient and stereoselctive synthesis of (Z)-β-(tosyloxy)alkenyl iodide has been developed from (aryl)[(E)-(β-tosyloxy)alkenyl]iodonium tosylates by using cheap cuprous chloride as the catalyst. A variety of trisubstituted alkenes have been prepared by sequential Suzuki coupling reactions of the alkenyl iodide products.

  9. Full Papers

    1. Nitrogen Heterocycles

      Synthetic Route to Rare Isoindolones Derivatives

      Killian Oukoloff, Frédéric Buron, Sylvain Routier, Ludovic Jean and Pierre-Yves Renard

      Article first published online: 23 FEB 2015 | DOI: 10.1002/ejoc.201403649

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      A shorter and more versatile synthetic route has been developed to prepare tetrahydropyrido[2,1-a]isoindolone and superior analogues. The key step of this synthesis is the formation of the lactam ring by a cyclization using Shibasaki's conditions.

    2. Chiral Ionic Liquids

      Coordinating Chiral Ionic Liquids: Design, Synthesis, and Application in Asymmetric Transfer Hydrogenation under Aqueous Conditions

      Maria Vasiloiu, Peter Gaertner, Ronald Zirbs and Katharina Bica

      Article first published online: 20 FEB 2015 | DOI: 10.1002/ejoc.201403555

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      The ruthenium-catalyzed asymmetric transfer hydrogenation of aromatic ketones was carried out under aqueous conditions by using a hydrophilic chiral ionic liquids with an amino alcohol substructure as the sole source of chirality. When used in the reaction system, these chiral ionic liquids provided high yields and excellent selectivities.

    3. 1,3-Dienes

      General Preparation of 1-Substituted (E)-1,3-Dienes under Mild Conditions

      Raquel G. Soengas, Humberto Rodríguez-Solla, Ainhoa Díaz-Pardo, Rita Acúrcio, Carmen Concellón, Vicente del Amo and Artur M. S. Silva

      Article first published online: 20 FEB 2015 | DOI: 10.1002/ejoc.201403623

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      A mild, straightforward and simple method to obtain 1-substituted (E)-1,3-dienes from very diverse functionalized aldehydes is reported. The procedure is based on the metal-promoted reductive β-elimination of 2-chloroallyl acetates, derived from aldehydes. Both In/CuI and Mg/ZnCl2 efficiently gave the dienes in good yields and with good to high stereoselectivities.

    4. Chromophores

      Stimuli-Responsive Cyclopenta[ef]heptalenes: Synthesis and Optical Properties

      Ebrahim H. Ghazvini Zadeh, Adam W. Woodward, David Richardson, Mykhailo. V. Bondar and Kevin D. Belfield

      Article first published online: 19 FEB 2015 | DOI: 10.1002/ejoc.201500059

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      Cyclopenta[ef]heptalenes 4ac, prepared by annulation of 3-formylguaiazulene (1), revealed a stimuli-responsive behavior upon treatment with strong acids. 1D and 2D NMR spectroscopy indicated that protonation occurred on C-6, while photoacid titrations demonstrated that the reported tricyclic systems can serve as efficient visible sensitizers of UV-activated photoacid generators (PAGs).

    5. Gold Nanopartilcles

      Dispersed Gold Nanoparticles Supported in the Pores of Siliceous Mesocellular Foam: A Catalyst for Cycloisomerization of Alkynoic Acids to γ-Alkylidene Lactones

      Kristofer Eriksson, Oscar Verho, Leif Nyholm, Sven Oscarsson and Jan-E. Bäckvall

      Article first published online: 19 FEB 2015 | DOI: 10.1002/ejoc.201403664

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      An electrochemical method for generating heterogeneously supported AuI thiolates that can be reduced to highly active Au nanoparticles by subsequent treatment with NaBH4 is described. The corresponding Au nanocatalyst was applied in the cycloisomerization of a set of alkynoic acids into the corresponding γ-alkylidene lactones in high yields under mild conditions.

    6. Pyridylpurine Nucleosides

      Synthesis of C6-Pyridylpurine Nucleosides by Reaction of Nebularine N1-Oxide with Pyridinyl Grignard Reagents

      Stefano D'Errico, Giorgia Oliviero, Nicola Borbone, Fabrizia Nici, Vincenzo Piccialli, Brunella Pinto, Daniele D'Alonzo, Luciano Mayol and Gennaro Piccialli

      Article first published online: 19 FEB 2015 | DOI: 10.1002/ejoc.201403648

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      The synthesis of a set of C6-pyridylpurine nucleosides is reported, exploiting the reactivity of nebularine N1-oxide towards pyridinyl Grignard reagents.

    7. Polycationic Fullerene Derivative

      Formation of Highly Charged Quasi-Molecular Ions of a Polycationic [60]Fullerene Hexakis-Adduct and Their Fragmentation Behavior in the Gas Phase

      Jing Li, Leanne C. Nye, Lennard K. Wasserthal, Chau Vinh, Rolf W. Kirschbaum, Ivana Ivanović-Burmazović, Andreas Hirsch and Thomas Drewello

      Article first published online: 19 FEB 2015 | DOI: 10.1002/ejoc.201500102

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      A novel polycationic [60]fullerene hexakis-adduct (12 pre-formed charges) has been synthesized and investigated by electrospray ionization and tandem mass spectrometry. The polycation showed neutral losses and Coulomb explosions.

    8. Tandem Reactions

      Lewis-Acid-Catalysed Tandem Meinwald Rearrangement/Intermolecular [3+2]-Cycloaddition of Epoxides with Donor–Acceptor Cyclopropanes: Synthesis of Functionalized Tetrahydrofurans

      Ashok Kumar Pandey, Asit Ghosh and Prabal Banerjee

      Article first published online: 19 FEB 2015 | DOI: 10.1002/ejoc.201403590

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      A Lewis-acid-catalysed tandem Meinwald rearrangement/[3+2]-cycloaddition of epoxides with donor–acceptor cyclopropanes to synthesize varieties of cis-2,5-aryl-benzyl-substituted tetrahydrofurans is described. An enantioselective version of the same transformation is also presented using various BOX ligands.

    9. Solid-State Halogenation

      Trihaloisocyanuric Acids as Atom-Economic Reagents for Halogenation of Aromatics and Carbonyl Compounds in the Solid State by Ball Milling

      Abhaya K. Mishra, Honnappa Nagarajaiah and Jarugu Narasimha Moorthy

      Article first published online: 19 FEB 2015 | DOI: 10.1002/ejoc.201403463

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      Trihaloisocyanuric acids are shown to serve as excellent reagents for the facile, solvent-free halogenation of aromatics and carbonyl compounds under ball-milling conditions at room temperature.

    10. Protein–Ligand Interactions

      High Affinity Fluorescent Ligands for the Estrogen Receptor

      Frank Abendroth, Marthe Solleder, Dorothea Mangoldt, Pia Welker, Kai Licha, Marcus Weber and Oliver Seitz

      Article first published online: 19 FEB 2015 | DOI: 10.1002/ejoc.201403489

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      Dual click reactions have facilitated hydrophobic tagging of selective estrogen receptor modulators (SERMs). Raloxifene conjugation with fluorescent dyes afforded fluorescent ER with affinities superior to estradiol. These stains accumulate in ER expressing cells at low nanomolar concentrations and molecular dynamics simulations suggest dye–ER associations via helix 12 contacts.

    11. Chromophores

      Benz-Bisimidazole-Bridged Perylenes – Linearly Expanded Chromophores

      Jörg Schönamsgruber and Andreas Hirsch

      Article first published online: 19 FEB 2015 | DOI: 10.1002/ejoc.201403561

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      We present the synthesis and characterization of a new type of perylene chromophore. Two perylene moieties are combined to form an overall conjugated π system. Parts of the molecule could be protonated and, thereby, the absorption and fluorescence emission spectra shifted bathochromically. The electronic band gap was determined to be 1.33–1.35 eV.

    12. Alkaloid Synthesis

      Synthesis of Condensed Tetrahydroisoquinoline Class of Alkaloids by Employing TfOH-Mediated Imide Carbonyl Activation

      Jayaraman Selvakumar, Ramana Sreenivasa Rao, Vijayan Srinivasapriyan, Srinivasan Marutheeswaran and Chinnasamy Ramaraj Ramanathan

      Article first published online: 19 FEB 2015 | DOI: 10.1002/ejoc.201403617

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      The isoquinoline-based polycyclic lactams and simple isoquinoline alkaloids were successfully assembled from the corresponding imides by using a TfOH-mediated (TfOH = trifluoromethanesulfonic acid) imide carbonyl activation and cyclization strategy. The regioselective cyclization of unsymmetrical phenethylimides with TfOH was studied by experimental and computational methods.

  10. Short Communications

    1. Suzuki–Miyaura Reactions

      The Suzuki–Miyaura Reaction Performed Using a Palladium–N-Heterocyclic Carb­ene Catalyst and a Weak Inorganic Base

      Frédéric Izquierdo, Martin Corpet and Steven P. Nolan

      Article first published online: 18 FEB 2015 | DOI: 10.1002/ejoc.201500043

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      [Pd(IPr)(cin)Cl] permits an operationally simple Suzuki–Miyaura reaction under very mild conditions using a mixture of ethanol/water as solvent and an inorganic base.

  11. Full Papers

    1. Acidity

      Are Benzoic Acids Always More Acidic Than Phenols? The Case of ortho-, meta-, and para-Hydroxybenzoic Acids

      Renan S. Galaverna, Giovana A. Bataglion, Gabriel Heerdt, Gilberto F. de Sa, Romeu Daroda, Valnei S. Cunha, Nelson H. Morgon and Marcos N. Eberlin

      Article first published online: 18 FEB 2015 | DOI: 10.1002/ejoc.201403528

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      Solvent and counterion effects operate in solution to make benzoic acids far more acidic than phenols, but in the gas phase, as shown herein for model bifunctional ortho-, meta-, and para-hydroxybenzoic acids, the acidities are close, and care should, therefore, be taken in predicting acidity orders. Values are close and are affected by interfering inductive, resonance, and/or H-bonding effects.

    2. Natural Products

      Asymmetric Synthesis of Concentricolide

      Xiaojing Liu, Lingling Hu, Lizhen Jiang, Junhao Jia, Di Zhang and Xiaochuan Chen

      Article first published online: 18 FEB 2015 | DOI: 10.1002/ejoc.201403604

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      A practical strategy for the synthesis of both (–)- and (+)-concentricolide from salicylic acid has been developed. The key step of the approach is sequential ortho-lithiation on the aryl ring and condensation with aldehyde aided by stereocontrol through a chiral oxazoline derived from L- or D-phenylalaninol.

    3. Reductive Monoalkylation

      Indium(III)-Catalyzed Reductive Mono­alkylation of Electron-Rich Benzenes with Aliphatic Carboxylic Acids Leading to Arylalkane Derivatives

      Toshimitsu Moriya, Kentaro Takayama, Takeo Konakahara, Yohei Ogiwara and Norio Sakai

      Article first published online: 18 FEB 2015 | DOI: 10.1002/ejoc.201500096

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      A combination of InI3, 1,1,3,3-tetramethyldisiloxane (TMDS), and molecular iodine effectively undergoes one-pot monoalkylation of electron-rich benzene derivatives with aliphatic carboxylic acids having a variety of substituents, leading to the preparation of arylated alkane derivatives.

  12. Short Communications

    1. Biomimetic Synthesis

      Biomimetic Assembly of Leucoridine A

      Sarah Benayad, Mehdi A. Beniddir, Laurent Evanno and Erwan Poupon

      Article first published online: 17 FEB 2015 | DOI: 10.1002/ejoc.201500041

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      The biomimetic cascade assembly of leucoridine A, a pseudosymmetric bisindole of Leuconotis griffithi (Apocynaceae) is described. The semisynthetic route provides suitable conditions toward the central 3-spiro-1,2,3,4-tetrahydropiperidine ring connecting the two subunits of the highly congested structure. The biomimetic assembly by an imino-Rauhut–Currier reaction affords the natural (S)-diastereomer of leucoridine A as the sole product.

  13. Full Papers

    1. Conjugated Systems

      Swivel-Cruciform Stilbenes Based on Bithiophene

      Amaranda García-Rodríguez, Antonio M. Rodríguez, Pilar Prieto, Raquel Andreu, Sonia Merino and Julián Rodríguez-López

      Article first published online: 17 FEB 2015 | DOI: 10.1002/ejoc.201500071

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      Bithiophene-based cruciforms with stilbenoid arms at the 3,3′- and 5,5′-positions adopt a twisted geometry owing to steric hindrance between the stilbene arms. This results in weaker intermolecular interactions and better solubility in common solvents. Electrochemical results demonstrate that these systems can support radical cations and show their potential as hole-transporting materials.

    2. Alkaloid Synthesis

      Synthesis of (–)-Cryptopleurine by Combining Gold(I) Catalysis with a Free Radical Cyclization

      Alexander Stoye and Till Opatz

      Article first published online: 17 FEB 2015 | DOI: 10.1002/ejoc.201403700

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      (R)-(–)-Cryptopleurine, a highly bioactive phenanthroquinolizidine alkaloid, was synthesized in high optical purity using a combination of gold(I)-NHC catalyzed regioselective ring closure of an unsymmetrical phenanthrene precursor and free radical cyclization chemistry to install ring C in the penultimate step.

    3. Flavonoids

      The First Total Synthesis of Sophoflavescenol, Flavenochromane C, and Citrusinol

      Van-Son Nguyen, Lin-Pei Dong, Sheng-Chun Wang and Qiuan Wang

      Article first published online: 17 FEB 2015 | DOI: 10.1002/ejoc.201403689

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      The first total syntheses of sophoflavescenol, flavenochromane C, and citrusinol were achieved in 23, 17, and 16 % yields, respectively, starting from 2,4,6-trihydroxyacetophenone and substituted benzaldehydes. The key step was a regioselective microwave-assisted Claisen rearrangement to form an 8-prenylated flavonoid from a 5-O-prenylflavonoid.

    4. Natural Products

      Oximoaspergillimide, a Fungal Derivative from a Marine Isolate of Aspergillus sp.

      Faviola Cardoso-Martínez, José M. de la Rosa, Ana R. Díaz-Marrero, José Darias, Luis D'Croz, Claudia Cerella, Marc Diederich and Mercedes Cueto

      Article first published online: 17 FEB 2015 | DOI: 10.1002/ejoc.201403668

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      Oximoaspergillimide (1), a new alkaloid derivative, was isolated from a cultured marine-derived fungus (strain CF07002) identified as a member of the genus Aspergillus. Oximoaspergillimide (1) is the first natural product reported to contain an oxime–imide functionality.

    5. First Enantioselective Synthesis of Marine Diterpene Ambliol-A

      Stefano Serra and Veronica Lissoni

      Article first published online: 17 FEB 2015 | DOI: 10.1002/ejoc.201403610

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      The enantioselective synthesis of diterpene (+)-ambliol-A and diastereoselective synthesis of its non-natural epimer are accomplished from racemic α-ionone. The key steps are diastereoselective epoxidation, lipase-mediated resolution, and copper-catalyzed cross coupling. The chemical structure of natural ambliol-A is confirmed and its absolute configuration corrected and now assigned as (1R,2R).

    6. Asymmetric Catalysis

      Olefin Hydrogenation with Rigid Mono-P-stereogenic Diphosphines: A Flexible Rhodium Ring to Rule Them All?

      Slavko Rast, Michel Stephan and Barbara Mohar

      Article first published online: 17 FEB 2015 | DOI: 10.1002/ejoc.201403570

      Thumbnail image of graphical abstract

      P-(o-Ph2P-Ph)-based P-stereogenic diphosphines prepared through the Jugé–Stephan route were studied in the RhI-catalyzed hydrogenation of olefins. For the first time, retention of P-configuration was observed in the methanolysis step. This rigid design brought further mechanistic insights on the relationship between steric and electronic factors of related C2-symmetric P,P,P′,P′-tetraarylic CH2CH2-bridged ligands.

  14. Short Communications

    1. Azetidine Synthesis

      A Mild and Selective Reduction of β-­Lactams: Rh-Catalyzed Hydrosilylation towards Important Pharmacological Building Blocks

      Christoph Bornschein, Alastair J. J. Lennox, Svenja Werkmeister, Kathrin Junge and Matthias Beller

      Article first published online: 17 FEB 2015 | DOI: 10.1002/ejoc.201403655

      Thumbnail image of graphical abstract

      A selective Rh-catalyzed protocol to reduce β-lactams to important pharmacologically active azetidines is presented. Reaction with tertiary amides was selective over secondary amides, esters, olefins and nitriles, with no erosion of stereochemistry. A one-pot protocol from commercially available starting materials and a selective reduction of a complex penicillin derivative demonstrate the high synthetic utility of this procedure.

  15. Full Papers

    1. Aminocarbonylation

      Palladium-Catalyzed Oxidative Aminocarbonylation by Decarboxylative Coupling: Synthesis of Alkynyl Amides

      Jinil Hwang, Jinseop Choi, Kyungho Park, Wonyoung Kim, Kwang Ho Song and Sunwoo Lee

      Article first published online: 16 FEB 2015 | DOI: 10.1002/ejoc.201403644

      Thumbnail image of graphical abstract

      Alkynyl amides were synthesized from a palladium-catalyzed coupling reaction of alkynyl carboxylic acids and amines under carbon monoxide. The reactions were conducted with palladium(II) acetate and silver(I) oxide in acetonitrile at 80 °C for 1 h. This method provides good to moderate product yields and good functional group tolerance towards ketone, ester, and nitrile groups.

  16. Short Communications

    1. Pyrrole Synthesis

      Copper(II)-Catalyzed [4+1] Annulation of Propargylamines with N,O-Acetals: Entry to the Synthesis of Polysubstituted Pyrrole Derivatives

      Norio Sakai, Hiroaki Hori and Yohei Ogiwara

      Article first published online: 16 FEB 2015 | DOI: 10.1002/ejoc.201500098

      Thumbnail image of graphical abstract

      A CuCl2-catalyzed [4+1] annulation of propargylamines with N,O-acetals having an ester, a ketone, and an amide moiety, leading to the facile preparation of polysubstituted pyrrole derivatives is presented. This annulation series was achieved through 5-endo-dig cyclization and subsequent aromatization in one pot.

    2. Oxidative Coupling

      Synthesis of 2-Acylphenol and Flavene Derivatives from the Ruthenium-Catalyzed Oxidative C–H Acylation of Phenols with Aldehydes

      Hanbin Lee and Chae S. Yi

      Article first published online: 16 FEB 2015 | DOI: 10.1002/ejoc.201403518

      Thumbnail image of graphical abstract

      A cationic ruthenium hydride complex catalyzes the oxidative C–H coupling of phenols with aldehydes to form 2-acylphenol and flavene derivatives.

  17. Full Papers

    1. Amino Acids

      Cross-Claisen Condensation of N-Fmoc-Amino Acids – A Short Route to Heterocyclic γ-Amino Acids

      Loïc Mathieu, Clément Bonnel, Nicolas Masurier, Ludovic T. Maillard, Jean Martinez and Vincent Lisowski

      Article first published online: 16 FEB 2015 | DOI: 10.1002/ejoc.201500012

      Thumbnail image of graphical abstract

      Cross-Claisen condensations between N-Fmoc-amino acids and sterically hindered 1,1-dimethylallyl acetate provide a short route to 4-amino(methyl)-1,3-thiazole-5-carboxylic acids (ATCs), a new class of constrained heterocyclic γ-amino acids built around a thiazole ring. A wide variety of lateral chains can be introduced on the γ-carbon atom or on the thiazole core.

    2. Synthesis Design

      Conformationally Constrained Penta(hetero)cyclic Molecular Architectures by Photoassisted Diversity-Oriented Synthesis

      Weston J. Umstead, Olga A. Mukhina and Andrei G. Kutateladze

      Article first published online: 16 FEB 2015 | DOI: 10.1002/ejoc.201403620

      Thumbnail image of graphical abstract

      Intramolecular cycloadditions of photogenerated azaxylylenes in conjunction with straightforward postphotochemical transformations of the primary photoproducts provide access to unprecedented polyheterocyclic scaffolds possessing a minimal number of rotatable bonds and a high content of sp3-hybridized carbon atoms.

  18. Short Communications

    1. Iron Catalysis

      Chiral (Cyclopentadienone)iron Complexes for the Catalytic Asymmetric Hydrogenation of Ketones

      Piotr Gajewski, Marc Renom-Carrasco, Sofia Vailati Facchini, Luca Pignataro, Laurent Lefort, Johannes G. de Vries, Raffaella Ferraccioli, Alessandra Forni, Umberto Piarulli and Cesare Gennari

      Article first published online: 13 FEB 2015 | DOI: 10.1002/ejoc.201500146

      Thumbnail image of graphical abstract

      Reducto! Chiral (cyclopentadienone)iron complexes were synthesized and tested, after in situ activation, in the catalytic asymmetric hydrogenation of ketones leading to the highest enantiomeric excesses ever obtained with this type of catalysts.

  19. Full Papers

    1. Peptides

      Stabilization of a Natural β-Hairpin by a Twist-Compatible β-Turn Mimetic

      Matthias Körling and Armin Geyer

      Article first published online: 13 FEB 2015 | DOI: 10.1002/ejoc.201500048

      Thumbnail image of graphical abstract

      β-Hairpins detached from their natural protein environment usually lose their well-defined shape, although they fulfill all requirements to fold into a highly twisted hairpin peptide. In this study, two stabilization strategies from either end of the antiparallel β-strands, which reconstitute the shape of the discrete hairpin, are opposed to each other. The twist compatible β-turn mimetic Hot=Tap is shown to be superior to macrocyclic disulfides.

    2. Molecular Diversity

      One-Pot Domino Synthesis of Polyfunctionalized Benzophenones, Dihydroxanthones, and m-Terphenyls from 2-(Polyfluoroalkyl)chromones

      Vyacheslav Ya. Sosnovskikh, Vladislav Yu. Korotaev, Alexey Yu. Barkov, Igor B. Kutyashev and Alexander V. Safrygin

      Article first published online: 13 FEB 2015 | DOI: 10.1002/ejoc.201403585

      Thumbnail image of graphical abstract

      Reactions between 2-(polyfluoroalkyl)chromones and 2-(1-phenylalkylidene)malononitriles or ethyl α-cyano-β-methylcinnamate, leading variously to polyfunctionalized benzophenones, dihydroxanthones, or m-terphenyls, were investigated.

    3. Domino Michael Reactions

      Asymmetric Organocatalytic Synthesis of Highly Substituted Cyclohexenols by Domino Double-Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles

      Yeong-Jiunn Jang, Yu-Shan Chen, Chia-Jui Lee, Chi-Han Chen, Ganapuram Madhusudhan Reddy, Chi-Ting Ko and Wenwei Lin

      Article first published online: 12 FEB 2015 | DOI: 10.1002/ejoc.201403677

      Thumbnail image of graphical abstract

      An effective asymmetric organocatalytic synthesis of polysubstituted cyclohexenes from 1-hydroxy-1,4-dien-3-ones and 2-alkylidenemalononitriles by a domino double-Michael reaction sequence using quinine as catalyst has been achieved. The products were obtained in moderate-to-good yields (up to 96 %) and enantioselectivities (up to 92 % ee).

    4. Oxathiane Nucleosides

      Synthesis, Structure, and Conformational Analysis of Nucleoside Analogues Comprising Six-Membered 1,3-Oxathiane Sugar Rings

      Hala Abou Assi, Saúl Martínez-Montero, Dilip M. Dixit, Zhijie Chua, D. Scott Bohle and Masad J. Damha

      Article first published online: 12 FEB 2015 | DOI: 10.1002/ejoc.201403642

      Thumbnail image of graphical abstract

      Herein we report the synthesis and characterization of a novel class of nucleoside analogues comprising six-membered 1,3-oxathiane sugar rings. The conformations were identified by extensive NMR analysis and the X-ray structure of analogue 16 shows that the 1,3-oxathiane moiety adopts a chair conformation with the substituents located in equatorial positions.

  20. Short Communications

    1. Radical Arylation

      Benzoyl Peroxide Promoted Radical ortho-Alkylation of Nitrogen Heteroaromatics with Simple Alkanes and Alcohols

      Lei Fang, Liangshun Chen, Jianjun Yu and Limin Wang

      Article first published online: 12 FEB 2015 | DOI: 10.1002/ejoc.201403479

      Thumbnail image of graphical abstract

      A catalytic amount of benzoyl peroxide (BPO)-initiated cross-dehydrogenative coupling reaction of N-iminopyridine ylides with simple alkanes and alcohols has been developed. The strategy allowed convenient access to various 2-alkylpyridines in moderate to good yields without an additional reduction step to remove the activated group.

  21. Full Papers

    1. Reactivity Patterns

      On the Effect of Backbone Modifications in 3,3-Dimethyl-1-(trifluoromethyl)-3H-1λ3,2-benziodaoxole

      Nico Santschi, Coraline Matthey, Rino Schwenk, Elisabeth Otth and Antonio Togni

      Article first published online: 12 FEB 2015 | DOI: 10.1002/ejoc.201403634

      Thumbnail image of graphical abstract

      The reactivity of hypervalent-iodine-based trifluoromethylating agents, as expressed by the initial rate v0 in a model reaction, correlates to an easily determined physical parameter p, a 13C NMR chemical shift.

    2. Organocatalysis

      One-Pot Enantioselective Synthesis of 1,4-Naphthoquinone-Derived Polycycles through Oxidative Dearomatization and Aminocatalysis

      Loïc Pantaine, Vincent Coeffard, Xavier Moreau and Christine Greck

      Article first published online: 12 FEB 2015 | DOI: 10.1002/ejoc.201403597

      Thumbnail image of graphical abstract

      The asymmetric synthesis of diversely substituted 1,4-naphthoquinone-derived polycycles is described by merging dearomatization and aminocatalysis in a single vessel. The dearomatization step is promoted by PhI(OAc)2 or oxygen in the presence of a bodipy photosensitizer and two products are selectively isolated depending on the dienal substitution.

    3. Chromophores

      Synthesis, Properties, and Redox Behavior of Tris(1-azulenyltetracyanobutadiene) and Tris[1-azulenylbis(tetracyanobutadiene)] Chromophores Connected to a 1,3,5-Tri(1-azulenyl)benzene Core

      Taku Shoji, Akifumi Maruyama, Erika Shimomura, Daichi Nagai, Shunji Ito, Tetsuo Okujima and Kozo Toyota

      Article first published online: 12 FEB 2015 | DOI: 10.1002/ejoc.201403556

      Thumbnail image of graphical abstract

      Tris(1-azulenyltetracyanobutadiene) and tris[1-azulenylbis(tetracyanobutadiene)] chromophores with a C3-symmetrical structure are prepared by the formal [2+2] cycloaddition–retroelectrocyclization reactions of tetracyanoethylene (TCNE) with the corresponding alkynes, and their redox behavior is examined by CV, differential pulse voltammetry (DPV), and spectroelectrochemical measurements.

    4. Bicyclic Isoxazolidines

      Cycloaddition Reactions of Alkyl Cyclopropenecarboxylates Generated in situ with Nitrones: Construction of Substituted Pyrroles and 1,2-Oxazinanes

      Junhao Hu, Min Zhang and Yuefa Gong

      Article first published online: 11 FEB 2015 | DOI: 10.1002/ejoc.201403551

      Thumbnail image of graphical abstract

      A highly regioselective [3+2] cycloaddition of nitrones to alkyl 2-aroylcyclopropenecarboxylates is reported. The reactions proceeded readily to afford ring-fused isoxazolidines in moderate-to-high yields. The strained ring-fused cycloaddition products were selectively transformed into the corresponding polysubstituted pyrroles by N–O bond cleavage or 1,2-oxazinanes by ring-opening.

    5. Hydroaminomethylation

      Homogeneous and Semi-Heterogeneous Magnetically Retrievable Bis-N-Heterocyclic Carbene Rhodium(I) Based Catalysts for Selective Hydroaminomethylation Reactions

      Bishnu Dutta, Rony Schwarz, Suheir Omar, Suzana Natour and Raed Abu-Reziq

      Article first published online: 11 FEB 2015 | DOI: 10.1002/ejoc.201403526

      Thumbnail image of graphical abstract

      Various bis-N-heterocyclic carbene (bis-NHC) ligands are prepared and complexed with rhodium(I). Some of these complexes show excellent reactivity and high selectivity in homogeneous hydroaminomethylation reactions. A bis-NHC ligand derivative is supported on magnetite nanoparticles and after complexation with RhI is was applied successfully in semi-heterogeneous hydroaminomethylations.

    6. Nitration

      Effective Nitration of Anilides and Acrylamides by tert-Butyl Nitrite

      Yi-fei Ji, Hong Yan and Qi-bai Jiang

      Article first published online: 11 FEB 2015 | DOI: 10.1002/ejoc.201403510

      Thumbnail image of graphical abstract

      The efficient nitration of both anilides and acrylamides was achieved by using TBN (tert-butyl nitrite) as a metal-free nitrating reagent. This synthetic method has many advantages such as mild reaction conditions, a fast reaction rate, good to excellent yields, and a broad substrate scope. Our investigation indicates that a nitro radical is involved in the reaction mechanism.

    7. A Tuned Bicyclic Proazaphosphatrane for Catalytically Enhanced N-Arylation Reactions with Aryl Chlorides

      So Han Kim, Min Kim, John G. Verkade and Youngjo Kim

      Article first published online: 9 FEB 2015 | DOI: 10.1002/ejoc.201403428

      Thumbnail image of graphical abstract

      An efficient palladium-catalyzed N-arylation reaction of amines under mild conditions with a tuned bicyclic proazaphosphatrane has been developed.

    8. Total Synthesis

      Isolation and Asymmetric Total Synthesis of Fungal Secondary Metabolite Hygrophorone B12

      Eileen Bette, Alexander Otto, Tobias Dräger, Kurt Merzweiler, Norbert Arnold, Ludger Wessjohann and Bernhard Westermann

      Article first published online: 9 FEB 2015 | DOI: 10.1002/ejoc.201403455

      Thumbnail image of graphical abstract

      Hygrophorone B12 was isolated from the fruiting bodies of Hygrophorus abieticola, and was synthesized in enantiomerically pure form using a Sharpless asymmetric dihydroxylation and two diastereoselective aldol-type reactions as the key steps. This approach enabled the unambiguous determination of the relative and absolute configuration of hygrophorones B for the first time.

    9. Natural Product Synthesis

      Synthesis of Simplified Halogenated Chondramide Derivatives with Strong Cytostatic Properties

      Dominic Becker and Uli Kazmaier

      Article first published online: 9 FEB 2015 | DOI: 10.1002/ejoc.201403577

      Thumbnail image of graphical abstract

      Easily available dichlorinated Chondramide derivatives show high antitumor-activity towards selected cancer cell lines.

    10. Aromatic Nitriles

      Facile One-Pot Transformation of Arenes into Aromatic Nitriles under Metal-Cyanide-Free Conditions

      Toshiyuki Tamura, Katsuhiko Moriyama and Hideo Togo

      Article first published online: 9 FEB 2015 | DOI: 10.1002/ejoc.201403672

      Thumbnail image of graphical abstract

      Various electron-rich arenes could be effectively converted into the corresponding aromatic nitriles in good yields, by treatment with ZnBr2 and dichloromethyl methyl ether, followed by reaction with molecular iodine and aq. ammonia.

    11. Multicomponent Reactions

      Stereoselective Synthesis of Highly Functionalized Dispirooxindoles through [3+2] Cycloaddition of Carbonyl Ylides with 3-Arylideneoxindoles

      Basi V. Subba Reddy, Govindaraju Karthik, Tamilselvan Rajasekaran and Balasubramanian Sridhar

      Article first published online: 9 FEB 2015 | DOI: 10.1002/ejoc.201500002

      Thumbnail image of graphical abstract

      A highly stereoselective synthesis of furo-dispirooxindoles has been achieved by using 5 mol-% of Rh2(OAc)4 under mild conditions through 1,3-dipolar cycloaddition of 3-arylideneoxindoles, with carbonyl ylides that are generated from 3-diazooxindole and aldehyde.

    12. Palladium Catalysis

      Efficient and Versatile Buchwald–Hartwig Amination of (Hetero)aryl Chlorides Using the Pd–PEPPSI-IPr(NMe2)2 Precatalyst in the Presence of Carbonate Base

      Yin Zhang, Vincent César and Guy Lavigne

      Article first published online: 9 FEB 2015 | DOI: 10.1002/ejoc.201500030

      Thumbnail image of graphical abstract

      The Palladium precatalyst Pd–PEPPSI-IPr(NMe2)2, whose supporting N-heterocyclic carbene ligand was decorated with two dimethylamino groups, was found to catalyse the Buchwald–Hartwig amination of aryl halides with a wide range of amines under mild conditions using cesium carbonate as base.

    13. Cascade Reactions

      Divergent Cascade Construction of Skeletally Diverse “Privileged” Pyrazole-Derived Molecular Architectures

      Yongqiang Zhang, Shanchao Wu, Shengzheng Wang, Kun Fang, Guoqiang Dong, Na Liu, Zhenyuan Miao, Jianzhong Yao, Jian Li, Wannian Zhang, Chunquan Sheng and Wei Wang

      Article first published online: 5 FEB 2015 | DOI: 10.1002/ejoc.201403673

      Thumbnail image of graphical abstract

      A powerful divergent cascade strategy has been developed for the rapid construction of five distinct diverse enantioenriched pyrazole-derived scaffolds using only six simple building blocks. Furthermore, screening of 10 compounds exemplifying the five synthesized scaffolds revealed potent anticancer lead compounds.

    14. Perfluoroalkylated Quinolines

      CuII-Promoted Aerobic Cascade Reactions of 2-Alkynylanilines with Methyl Perfluoroalk-2-ynoates: En Route to 4-Carbonyl-2-perfluoroalkylquinolines

      Jing Han, Yangyong Shen, Xuechun Sun, Qiuxia Yao, Jie Chen, Hongmei Deng, Min Shao, Bozhen Fan, Hui Zhang and Weiguo Cao

      Article first published online: 5 FEB 2015 | DOI: 10.1002/ejoc.201403633

      Thumbnail image of graphical abstract

      Using air as the oxygen source, 4-carbonyl-2-perfluoroalkylquinolines were prepared in good to excellent yields from readily available 2-alkynylanilines and methyl perfluoroalk-2-ynoates through a CuII-promoted sequential process.

    15. Cascade Reactions

      A Cascade Aza-Cope/Aza-Prins Cyclization Leading to Piperidine Derivatives

      Jothi L. Nallasivam and Rodney A. Fernandes

      Article first published online: 5 FEB 2015 | DOI: 10.1002/ejoc.201403607

      Thumbnail image of graphical abstract

      The cascade aza-Cope/aza-Prins cyclization of homoallylamines to give substituted piperidines is described. A unimolecular tetrapiperidine derivative, which resulted from this strategy, was employed as a ligand in the Suzuki–Miyaura cross-coupling reaction of an α-iodobutenolide with an arylboronic acid in an efficient synthesis of incrustoporin and its analogues.

    16. Organocatalysis

      Chiral Phase-Transfer-Catalyzed Intramolecular aza-Michael Reactions for the Asymmetric Synthesis of Isoindolinones

      Stéphane Lebrun, Romain Sallio, Mélanie Dubois, Francine Agbossou-Niedercorn, Eric Deniau and Christophe Michon

      Article first published online: 5 FEB 2015 | DOI: 10.1002/ejoc.201403573

      Thumbnail image of graphical abstract

      Asymmetric intramolecular aza-Michael reactions with cinchoninium phase-transfer organocatalysts are used for the synthesis of optically active isoindolinones. The resulting compounds are useful intermediates for the synthesis and development of benzodiazepine-receptor agonists.

    17. Reductive Sulfidation

      Indium-Catalyzed Reductive Sulfidation of Aromatic Carboxylic Acids and Aldehydes with Elemental Sulfur to Prepare Symmetrical Benzyl Sulfides

      Takahiro Miyazaki, Kota Nishino, Shunsuke Yoshimoto, Yohei Ogiwara and Norio Sakai

      Article first published online: 5 FEB 2015 | DOI: 10.1002/ejoc.201403567

      Thumbnail image of graphical abstract

      The coupling reaction of either aromatic carboxylic acids or aromatic aldehydes with elemental sulfur in the presence of a catalytic amount of InI3 and TMDS effectively produced the corresponding symmetrical benzyl sulfide derivatives.

    18. Radical Decarboxylative Fluorination

      Radical Decarboxylative Fluorination of Aryloxyacetic Acids Using N-Fluorobenzenesulfonimide and a Photosensitizer

      Joe C. T. Leung and Glenn M. Sammis

      Article first published online: 5 FEB 2015 | DOI: 10.1002/ejoc.201500038

      Thumbnail image of graphical abstract

      Photodecarboxylative fluorination methodology involving the use of photosensitizers and N-fluorobenzenesulfonimide (NFSI) provides facile access to monofluoromethoxy-substituted arenes through the direct fluorodecarboxylation of carboxylic acids. Utilization of NFSI enables the synthesis of fluoromethyl ethers that were previously inaccessible with decarboxylative fluorinations performed with Selectfluor.

  22. Microreviews

    1. Difunctionalization of Alkynes

      Direct Vicinal Difunctionalization of Alkynes: An Efficient Approach Towards the Synthesis of Highly Functionalized Fluorinated Alkenes

      Tatiana Besset, Thomas Poisson and Xavier Pannecoucke

      Article first published online: 5 FEB 2015 | DOI: 10.1002/ejoc.201403507

      Thumbnail image of graphical abstract

      The concomitant introduction of fluorinated groups and an additional functional group into alkynes has attracted considerable attention as an efficient synthetic route towards polyfunctionalized fluorinated olefins. This microreview focuses on the major progress achieved in this field involving transition-metal-catalyzed transformations and radical processes.

    2. Synthesis of Azaheterocycles

      Furan's Gambit: Electrophile-Attack-Triggered Sacrifice of Furan Rings for the Intramolecular Construction of Azaheterocycles

      Igor V. Trushkov, Maxim G. Uchuskin and Alexander V. Butin

      Article first published online: 3 FEB 2015 | DOI: 10.1002/ejoc.201403580

      Thumbnail image of graphical abstract

      Chemistry is like chess! A gambit is a chess opening in which a player sacrifices something to achieve something else. The concept of the gambit is also used in organic chemistry. This review deals with intramolecular transformations pertaining to the sacrifice of a furan ring for the production of a variety of nitrogen heterocycles.

    3. Green Chemistry

      Chitosan: An Upgraded Polysaccharide Waste for Organocatalysis

      Olivier Mahé, Jean-François Brière and Isabelle Dez

      Article first published online: 29 JAN 2015 | DOI: 10.1002/ejoc.201403396

      Thumbnail image of graphical abstract

      This microreview outlines recent advances in achiral to asymmetric organocatalytic reactions based on chitosan, a biodegradable chiral polysaccharide obtained from marine wastes, in a sustainable chemistry context. The use of chitosan and its derivatives either as insoluble organocatalysts or as supports for organocatalysts is reviewed, together with shaping and reusability issues.

    4. Furopyridines

      Elaboration of Furopyridine Scaffolds

      Adeline Jasselin-Hinschberger, Corinne Comoy, Anthony Chartoire and Yves Fort

      Article first published online: 22 JAN 2015 | DOI: 10.1002/ejoc.201403412

      Thumbnail image of graphical abstract

      This review is focused on furopyridines and especially on the different strategies that allow their synthesis.

    5. Biologically Active Sesquiterpenes

      Trends in the Synthesis and Functionalization of Guaianolides

      Alejandro Santana, José M. G. Molinillo and Francisco A. Macías

      Article first published online: 15 JAN 2015 | DOI: 10.1002/ejoc.201403244

      Thumbnail image of graphical abstract

      Guaianolides and their derivatives display diverse biological activities and have for decades been targets for synthesis. Semi-synthesis, usually staring from eudemane sesquiterpenes, or total synthesis by use of an extensive range of synthetic methodologies to obtain the hydroazulene skeleton are the two principal strategies.

    6. Guanidine Derivatives

      Synthetic Strategies for Preparing Bicyclic Guanidines

      Barbora Lemrová and Miroslav Soural

      Article first published online: 5 JAN 2015 | DOI: 10.1002/ejoc.201403185

      Thumbnail image of graphical abstract

      Guanidine-based derivatives I with all three nitrogen atoms contained in two neighbouring cycles represent an interesting group of compounds with some unique properties. We describe the most important synthetic methods to prepare various target derivatives from different starting materials.

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